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There are, you could argue, two Clint Eastwoods. One is the strong, near-silent type, the man with no name but a pair of Colt revolvers or a .44 Magnum, the lean avenging angel who asks if you feel lucky, punk, and would care to make his day. Whether he's a tough cop, a tough cowboy, a tough secret-service agent, a tough military man, a tough experimental-jet-fighter pilot or a tough racist old coot, the part is a variation on Eastwood's screen persona. His status as a macho icon was cast in immovable granite early on; to many, Eastwood is still the man who wielded suggestively-long barreled guns and doled out ruthless justice to criminals and assorted thugs. He is Dirty Harry, by any other name.

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Then there's the Clint behind the camera, the classicist who evokes old-school filmmakers like John Ford and Eastwood's mentor Don Siegel, the guy who likes to keep things nice and easy on the set, and never likes to do more than a few takes. The director who makes movies that feel ambivalent about taking the law into your own hands, and biopics about jazz musicians, and a genuine tearjerker about a love between two late-in-life romantics that could not be. The serious gentleman who gets nominated for, and occasionally wins, Oscars. The Clint Eastwood who adapts a megapopular Broadway musical for the big screen.

This is the point when a large portion of moviegoers, even ones who know Eastwood's work as an auteur, may find themselves unconsciously asking: Wait, how the hell did Dirty Harry wind up directing a musical?!?

Jersey Boys, Eastwood's take on the hit show about the rise and fall of Frankie Valli and the Four Seasons, seems at first like unfamiliar terrain, and has understandably perplexed many who have seen the words "Directed by Clint Eastwood" in ads and trailers. In truth, Eastwood the director has flirted with the genre multiple times: There's Honkytonk Man(1982), in which he played a dying country singer making one last shot at the Grand Ole Opry; and there's Bird, (1988) his ambitious exploration of hard-bop great and musical genius Charlie Parker, starring Forest Whitaker. (The less said about Eastwood the actor's foray into musicals, 1969's Paint Your Wagon, the better.) In recent years, he has composed the scores for many of his films, including Mystic River (2003) and J. Edgar (2011). He sang the title song for Gran Torino (2008) and was nominated for a Golden Globe for it. And then, once upon a time, there was also this. So maybe we shouldn't be asking why "Dirty Harry" is directing a straight-up, old-fashioned musical – but rather why it's taken Clint so long to do so.

And, of course, Eastwood isn't starring in Jersey Boys. As he's gotten older, he's focused more on his efforts behind the camera than in front of it (with occasional pit stops into commercials and WTF-political-convention speeches). But his persona has regularly bled into and reverberated against his work as a filmmaker over the years. And the peculiar interplay between his stardom and his directorial career – between Dirty Harry and Clint — and the way they've converged and diverged in unexpected ways reveals a lot about who he is as an artist.

In his early years as a director, Eastwood's films consciously played to his cowboy/tough-guy image. But right from the start, they also interrogated it: High Plains Drifter (1973), the first Western he directed, could easily fit within the Man with No Name canon. But it's so relentlessly dark and brutal – the hero is virtually a rapist, and the townspeople he's "saving" a bunch of opportunistic, cowardly scum – that one finds it hard to feel any kind of satisfaction by the end of the film. The Outlaw Josey Wales (1976) starts off as a typical epic about revenge, but it builds up to a surprising finale, as, years later, Josey Wales and his nemesis part ways without firing a shot, acknowledging that the Civil War is long over. Neither of these films could really be called "revisionist Westerns," but they're clearly the work of someone who already wants to push the lonesome cowboy mythos in interesting, even unsettling ways.

What's acknowledged by many as the actor-director's masterpiece, however, is a revisionist Western par excellence. Unforgiven (1992) gives us Eastwood's William Munny, a retired outlaw who has taken one last job as a bounty hunter; he guns down his prey, who are often humanized in discomfiting ways. "It's a hell of a thing, killing a man," Munny says, philosophizing to an impressionable young man who has just taken his first life. "Take away all he's got and all he's ever gonna have." It's the kind of self-reflection that might have made Dirty Harrygag. And yet, delivered via Eastwood the star, the lines become not so much an appeal for humanity but a gruff, existential bit of prairie poetry.

He adds a powerful dimension to that film's follow-up as well: A Perfect World (1993), which stars Kevin Costner as Butch Haynes, a fugitive who kidnaps a young boy. Eastwood has a supporting role as Red Barnett, the Texas Ranger tasked with tracking them down — and, it turns out, was responsible for sending the troubled young Butch to an institution back in the day. His iconic presence takes a screenwriter's grace note and gives it mythic dimension. "Do I know you, friend?" Costner's wounded Butch asks Eastwood's Red when they finally meet at the end of the film, in a wide, empty meadow. "No, not really," responds the lawman, but his uncomfortable terseness betrays his remorse. The film suggests that Red's tough guy ethos may have had more than a little to do with Butch's present psychosis and tragic fate.

Eastwood's humanism is often more pronounced when he doesn't star in his films, when his presence doesn't focus all the attention on himself. His remarkable World War II diptych of Flags of Our Fathers and Letters from Iwo Jima (both 2006) offered lyrical ensemble stories portraying the alternately ennobling and corrosive effects of both victory and defeat. His flawed South African historical drama Invictus (2009) looks at the way that Nelson Mandela (Morgan Freeman) helped bring together a divided country through its national rugby team. And then there's Mystic River, Eastwood's award-winning adaptation of Dennis Lehane's novel about a grisly murder that tears apart a small Boston community – a grim, expansive meditation on the effects of violence on both the individual and society. Some of the advertising played up Eastwood's brand as an actor, with early trailers prominently featured his distinctive voice, talking about "fear, betrayal, and murder." It was a supreme irony: the unmistakable voice of Dirty Harry helping to sell a movie about the corrosive effects of vigilantism. Viewers might have been forgiven for thinking that this would be a thriller starring the man himself.

Eastwood played up this irony later in Gran Torino, in which he does star – as a gruff, xenophobic Korean veteran worried about the Hmong families moving into his neighborhood. At the end of the film, Eastwood martyrs himself by pretending to pull a gun on a group of armed gang-members. Justice, in this case, is meted out not by our aging hero, but by the police who round the thugs up for killing an old, unarmed man, and by the community of neighbors who witnessed the incident. It's a surprising way to end a movie that was practically sold asDirty Harry, Senior Citizen. But it makes symbolic sense: In order for the community to thrive and to continue, the Clint Eastwood figure – the disruptive loner, the man with no name and no place – has to die and go away.

So, where does that leave Jersey Boys? The music of the Four Seasons is a far cry from the jazz and blues music that Eastwood notably adores. But here, too, we have a tale of community, about four kids joining up to escape their rough neighborhood and make beautiful music together. So, maybe the best way to think about it is not so much a musical as a drama about the tension between tough surroundings – per the movie, Valli and co. came from a background of crime, prison stints, and mob connections – and the human desire to find tenderness and beauty. Clint Eastwood understands that tension. It's a song he's been singing for a long, long time.